NL8300159A - 3,3-dialkyl- en 3,3-alkyleen-indolinederivaten, werkwijzen voor het bereiden van deze derivaten en farmaceutische preparaten die ze bevatten. - Google Patents
3,3-dialkyl- en 3,3-alkyleen-indolinederivaten, werkwijzen voor het bereiden van deze derivaten en farmaceutische preparaten die ze bevatten. Download PDFInfo
- Publication number
- NL8300159A NL8300159A NL8300159A NL8300159A NL8300159A NL 8300159 A NL8300159 A NL 8300159A NL 8300159 A NL8300159 A NL 8300159A NL 8300159 A NL8300159 A NL 8300159A NL 8300159 A NL8300159 A NL 8300159A
- Authority
- NL
- Netherlands
- Prior art keywords
- indoline
- dimethyl
- group
- formula
- acid addition
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 21
- 239000000825 pharmaceutical preparation Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 47
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 30
- 239000012458 free base Substances 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000006239 protecting group Chemical group 0.000 claims description 18
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 230000010933 acylation Effects 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 238000005661 deetherification reaction Methods 0.000 claims description 8
- 238000005917 acylation reaction Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000010555 transalkylation reaction Methods 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- CNYMFJWCSOZAFV-UHFFFAOYSA-N 3,3-dimethyl-5-propan-2-yloxy-1,2-dihydroindole Chemical compound CC(C)OC1=CC=C2NCC(C)(C)C2=C1 CNYMFJWCSOZAFV-UHFFFAOYSA-N 0.000 claims description 3
- AYVGKVADTZHDDD-UHFFFAOYSA-N 5-ethoxy-3,3-dimethyl-1,2-dihydroindole Chemical compound CCOC1=CC=C2NCC(C)(C)C2=C1 AYVGKVADTZHDDD-UHFFFAOYSA-N 0.000 claims description 3
- QWHYSBHTCJIXPO-UHFFFAOYSA-N 5-methoxy-3,3-dimethyl-1h-indol-2-one Chemical compound COC1=CC=C2NC(=O)C(C)(C)C2=C1 QWHYSBHTCJIXPO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
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- UZGAUBROKVHOFS-UHFFFAOYSA-N (1-acetyl-2-oxo-3h-indol-4-yl) acetate Chemical compound CC(=O)OC1=CC=CC2=C1CC(=O)N2C(C)=O UZGAUBROKVHOFS-UHFFFAOYSA-N 0.000 claims description 2
- XEWDCQVTGOZKNH-UHFFFAOYSA-N 1-(3,3-dimethyl-5-propan-2-yloxy-2h-indol-1-yl)ethanone Chemical compound CC(C)OC1=CC=C2N(C(C)=O)CC(C)(C)C2=C1 XEWDCQVTGOZKNH-UHFFFAOYSA-N 0.000 claims description 2
- AFBOHIVNJUEYQE-UHFFFAOYSA-N 1-(5-hydroxy-3,3-dimethyl-2h-indol-1-yl)ethanone Chemical compound OC1=CC=C2N(C(=O)C)CC(C)(C)C2=C1 AFBOHIVNJUEYQE-UHFFFAOYSA-N 0.000 claims description 2
- UJTAWOIWCRBJTH-UHFFFAOYSA-N 1-(5-methoxy-3,3-dimethyl-2h-indol-1-yl)ethanone Chemical compound COC1=CC=C2N(C(C)=O)CC(C)(C)C2=C1 UJTAWOIWCRBJTH-UHFFFAOYSA-N 0.000 claims description 2
- PQNISEJDWVDVNK-UHFFFAOYSA-N 3,3-dimethyl-5-propan-2-yloxy-1h-indol-2-one Chemical compound CC(C)OC1=CC=C2NC(=O)C(C)(C)C2=C1 PQNISEJDWVDVNK-UHFFFAOYSA-N 0.000 claims description 2
- ZDLJMUHGWNWHCS-UHFFFAOYSA-N 4-hydroxy-3,3-dimethyl-1h-indol-2-one Chemical compound C1=CC(O)=C2C(C)(C)C(=O)NC2=C1 ZDLJMUHGWNWHCS-UHFFFAOYSA-N 0.000 claims description 2
- DLQFYVZWDIHNKX-UHFFFAOYSA-N 5-ethoxy-3,3,7-trimethyl-1,2-dihydroindole Chemical compound CC1=CC(OCC)=CC2=C1NCC2(C)C DLQFYVZWDIHNKX-UHFFFAOYSA-N 0.000 claims description 2
- NHHCJCXGSFXXAX-UHFFFAOYSA-N 5-hydroxy-3,3,7-trimethyl-1h-indol-2-one Chemical compound CC1=CC(O)=CC2=C1NC(=O)C2(C)C NHHCJCXGSFXXAX-UHFFFAOYSA-N 0.000 claims description 2
- IVMYKLYNZCWHTC-UHFFFAOYSA-N 5-hydroxy-3,3-dimethyl-1h-indol-2-one Chemical compound C1=C(O)C=C2C(C)(C)C(=O)NC2=C1 IVMYKLYNZCWHTC-UHFFFAOYSA-N 0.000 claims description 2
- XHKJBYFKLWRGFP-UHFFFAOYSA-N 5-methoxy-3,3,7-trimethyl-1h-indol-2-one Chemical compound CC1=CC(OC)=CC2=C1NC(=O)C2(C)C XHKJBYFKLWRGFP-UHFFFAOYSA-N 0.000 claims description 2
- IYNJZTHCVZTRNV-UHFFFAOYSA-N 6-ethoxy-3,3,5-trimethyl-1,2-dihydroindole Chemical compound C1=C(C)C(OCC)=CC2=C1C(C)(C)CN2 IYNJZTHCVZTRNV-UHFFFAOYSA-N 0.000 claims description 2
- LTQXKFWKDLQHPY-UHFFFAOYSA-N 6-ethoxy-3,3,5-trimethyl-1h-indol-2-one Chemical compound C1=C(C)C(OCC)=CC2=C1C(C)(C)C(=O)N2 LTQXKFWKDLQHPY-UHFFFAOYSA-N 0.000 claims description 2
- ITLRQEKXUKZTPG-UHFFFAOYSA-N 6-ethoxy-3,3-dimethyl-1,2-dihydroindole Chemical compound CCOC1=CC=C2C(C)(C)CNC2=C1 ITLRQEKXUKZTPG-UHFFFAOYSA-N 0.000 claims description 2
- HKWUUXHDZYJYLD-UHFFFAOYSA-N 6-ethoxy-3,3-dimethyl-1h-indol-2-one Chemical compound CCOC1=CC=C2C(C)(C)C(=O)NC2=C1 HKWUUXHDZYJYLD-UHFFFAOYSA-N 0.000 claims description 2
- ZMZSNUROGZUHAW-UHFFFAOYSA-N 6-hydroxy-3,3,5-trimethyl-1h-indol-2-one Chemical compound C1=C(O)C(C)=CC2=C1NC(=O)C2(C)C ZMZSNUROGZUHAW-UHFFFAOYSA-N 0.000 claims description 2
- WDJLZDPQGHTYKZ-UHFFFAOYSA-N 6-hydroxy-3,3-dimethyl-1h-indol-2-one Chemical compound OC1=CC=C2C(C)(C)C(=O)NC2=C1 WDJLZDPQGHTYKZ-UHFFFAOYSA-N 0.000 claims description 2
- HYVHHZQCEOYGLL-UHFFFAOYSA-N 7-ethoxy-3,3-dimethyl-1,2-dihydroindole Chemical compound CCOC1=CC=CC2=C1NCC2(C)C HYVHHZQCEOYGLL-UHFFFAOYSA-N 0.000 claims description 2
- KKIHSFZXMUNNIG-UHFFFAOYSA-N 7-ethoxy-3,3-dimethyl-1h-indol-2-one Chemical compound CCOC1=CC=CC2=C1NC(=O)C2(C)C KKIHSFZXMUNNIG-UHFFFAOYSA-N 0.000 claims description 2
- OAHKNTGVVFWRJJ-UHFFFAOYSA-N 7-hydroxy-3,3-dimethyl-1h-indol-2-one Chemical compound C1=CC=C(O)C2=C1C(C)(C)C(=O)N2 OAHKNTGVVFWRJJ-UHFFFAOYSA-N 0.000 claims description 2
- BHIXTFSJENSHBP-UHFFFAOYSA-N 7-methoxy-3,3-dimethyl-1h-indol-2-one Chemical compound COC1=CC=CC2=C1NC(=O)C2(C)C BHIXTFSJENSHBP-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- RKVQFFJTKLBNRP-UHFFFAOYSA-N 1-ethoxy-2,3-dihydroindole Chemical compound C1=CC=C2N(OCC)CCC2=C1 RKVQFFJTKLBNRP-UHFFFAOYSA-N 0.000 claims 1
- JWLQULBRUJIEHY-UHFFFAOYSA-N 2,3-dihydro-1h-indol-6-ol Chemical compound OC1=CC=C2CCNC2=C1 JWLQULBRUJIEHY-UHFFFAOYSA-N 0.000 claims 1
- CUTTYKZZUHMSJV-UHFFFAOYSA-N 3,3-dimethyl-6-propan-2-yloxy-1,2-dihydroindole Chemical compound CC(C)OC1=CC=C2C(C)(C)CNC2=C1 CUTTYKZZUHMSJV-UHFFFAOYSA-N 0.000 claims 1
- ZUFUJVPHGVWYAG-UHFFFAOYSA-N 3,3-dimethyl-6-propan-2-yloxy-1h-indol-2-one Chemical compound CC(C)OC1=CC=C2C(C)(C)C(=O)NC2=C1 ZUFUJVPHGVWYAG-UHFFFAOYSA-N 0.000 claims 1
- OCEMCBBMNJBAJI-UHFFFAOYSA-N 4-ethoxy-3,3-dimethyl-1,2-dihydroindole Chemical compound CCOC1=CC=CC2=C1C(C)(C)CN2 OCEMCBBMNJBAJI-UHFFFAOYSA-N 0.000 claims 1
- GQXQTKBIKOHVDS-UHFFFAOYSA-N 4-ethoxy-3,3-dimethyl-1h-indol-2-one Chemical compound CCOC1=CC=CC2=C1C(C)(C)C(=O)N2 GQXQTKBIKOHVDS-UHFFFAOYSA-N 0.000 claims 1
- KKXRYAPPQOIPCX-UHFFFAOYSA-N 5-methoxy-3,3,7-trimethyl-1,2-dihydroindole Chemical compound CC1=CC(OC)=CC2=C1NCC2(C)C KKXRYAPPQOIPCX-UHFFFAOYSA-N 0.000 claims 1
- 101150049033 haao gene Proteins 0.000 claims 1
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- 238000002844 melting Methods 0.000 description 35
- 230000008018 melting Effects 0.000 description 35
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- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
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- IGRJLJWPPSJVTG-UHFFFAOYSA-N 5-methoxy-1,3-dimethyl-2-nitrobenzene Chemical compound COC1=CC(C)=C([N+]([O-])=O)C(C)=C1 IGRJLJWPPSJVTG-UHFFFAOYSA-N 0.000 description 1
- ZCKUVSBCERFEKZ-UHFFFAOYSA-N 5-methoxy-7-methyl-1,3-dihydroindol-2-one Chemical compound CC1=CC(OC)=CC2=C1NC(=O)C2 ZCKUVSBCERFEKZ-UHFFFAOYSA-N 0.000 description 1
- HRINDOHVNYBEQJ-UHFFFAOYSA-N 5-propan-2-yloxy-1,3-dihydroindol-2-one Chemical compound CC(C)OC1=CC=C2NC(=O)CC2=C1 HRINDOHVNYBEQJ-UHFFFAOYSA-N 0.000 description 1
- APQCUXBFROFCOM-UHFFFAOYSA-N 7-methoxy-1,3-dihydroindol-2-one Chemical compound COC1=CC=CC2=C1NC(=O)C2 APQCUXBFROFCOM-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 235000007575 Calluna vulgaris Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 1
- 238000010934 O-alkylation reaction Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- KXNYJKMZLXNEJD-UHFFFAOYSA-N n-bromo-n-(3-hydroxy-4-methylphenyl)-2-methylpropanamide Chemical compound CC(C)C(=O)N(Br)C1=CC=C(C)C(O)=C1 KXNYJKMZLXNEJD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005690 transetherification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH37382 | 1982-01-21 | ||
| CH37382 | 1982-01-21 | ||
| CH374582 | 1982-06-17 | ||
| CH374582 | 1982-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8300159A true NL8300159A (nl) | 1983-08-16 |
Family
ID=25684383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8300159A NL8300159A (nl) | 1982-01-21 | 1983-01-17 | 3,3-dialkyl- en 3,3-alkyleen-indolinederivaten, werkwijzen voor het bereiden van deze derivaten en farmaceutische preparaten die ze bevatten. |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4622336A (en, 2012) |
| AT (1) | AT381490B (en, 2012) |
| AU (1) | AU565538B2 (en, 2012) |
| CA (1) | CA1191857A (en, 2012) |
| CH (1) | CH657848A5 (en, 2012) |
| CY (1) | CY1431A (en, 2012) |
| DE (1) | DE3300522A1 (en, 2012) |
| DK (1) | DK161071C (en, 2012) |
| ES (1) | ES519108A0 (en, 2012) |
| FI (1) | FI79098C (en, 2012) |
| FR (1) | FR2519982B1 (en, 2012) |
| GB (1) | GB2113682B (en, 2012) |
| HK (1) | HK56888A (en, 2012) |
| HU (1) | HU189215B (en, 2012) |
| IE (1) | IE54878B1 (en, 2012) |
| IL (1) | IL67715A (en, 2012) |
| IT (1) | IT1197546B (en, 2012) |
| KE (1) | KE3813A (en, 2012) |
| MY (1) | MY8600467A (en, 2012) |
| NL (1) | NL8300159A (en, 2012) |
| NZ (1) | NZ203056A (en, 2012) |
| PH (1) | PH22848A (en, 2012) |
| PT (1) | PT76110B (en, 2012) |
| SE (1) | SE453293B (en, 2012) |
| SG (1) | SG22688G (en, 2012) |
| WO (1) | WO1983002610A1 (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4690943A (en) * | 1984-09-19 | 1987-09-01 | Pfizer Inc. | Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds |
| US4803217A (en) * | 1986-12-24 | 1989-02-07 | Merck & Co., Inc. | Hapalindolinone compounds as vassopressin antagonists |
| GB8723157D0 (en) * | 1987-10-02 | 1987-11-04 | Beecham Group Plc | Compounds |
| GB9108965D0 (en) * | 1991-04-26 | 1991-06-12 | Sandoz Ltd | Improvements in or relating to organic compounds |
| FR2708606B1 (fr) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés du N-phénylalkylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
| WO2016179157A1 (en) | 2015-05-05 | 2016-11-10 | Carafe Drug Innovation, Llc | Substituted 5-hydroxyoxindoles and their use as analgesics and fever reducers |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE368009B (en, 2012) * | 1971-09-16 | 1974-06-17 | Kabi Ab | |
| AT311332B (de) * | 1971-12-06 | 1973-11-12 | Pierrel Spa | Verfahren zur Herstellung eines neuen Esters von 3,3-Bis(p-hydroxyphenyl)-2-indolinon und dessen Salzen |
| BE524637A (en, 2012) * | 1972-05-17 | |||
| GB1437804A (en) * | 1973-09-10 | 1976-06-03 | Lepetit Spa | Indole derivatives |
| AT346841B (de) * | 1976-11-30 | 1978-11-27 | Delmar Chem | Verfahren zur herstellung von neuen 3- phenylindolinen und ihren salzen |
| FI59246C (fi) * | 1974-06-24 | 1981-07-10 | Otsuka Pharma Co Ltd | Foerfarande foer framstaellning av benscykloamidderivat anvaendbara vid trombos- och emboliterapin |
| JPS597699B2 (ja) * | 1977-02-04 | 1984-02-20 | イハラケミカル工業株式会社 | インドリン類の製造方法 |
| DE2816380A1 (de) * | 1977-04-21 | 1978-12-07 | Hoechst Ag | Spiro eckige klammer auf indolin- 3,4'-piperidine eckige klammer zu und verwandte verbindungen |
| DE2805620A1 (de) * | 1978-02-10 | 1979-08-23 | Basf Ag | Verfahren zur herstellung von indoleninen |
| US4307235A (en) * | 1978-08-23 | 1981-12-22 | American Hoechst Corporation | Spiro[indoline-3,4'-piperidine]s |
| JPS597700B2 (ja) * | 1978-10-31 | 1984-02-20 | イハラケミカル工業株式会社 | インドリン類の製造方法 |
| US4408050A (en) * | 1980-02-15 | 1983-10-04 | American Hoechst Corporation | Spiro(indoline-3,4'-piperidine) and related compounds |
| US4345081A (en) * | 1980-02-15 | 1982-08-17 | American Hoechst Corporation | Spiro[indoline-3,4'-piperidine]s |
| DE3143327A1 (de) * | 1980-11-12 | 1982-06-09 | Dr. Karl Thomae Gmbh, 7950 Biberach | "neue indolinone, ihre herstellung und ihre verwendung als arzneimittel" |
| IT1143242B (it) * | 1980-11-18 | 1986-10-22 | Upjohn Co | 1,2,8,ba-ciclopropa(c)-benzo(1,2-b-4,3-b)dipirrol-4(5h)-one antibatte ricamente attivo e relativo metodo di preparazione |
-
1983
- 1983-01-10 DE DE19833300522 patent/DE3300522A1/de active Granted
- 1983-01-12 FR FR8300497A patent/FR2519982B1/fr not_active Expired
- 1983-01-14 FI FI830137A patent/FI79098C/fi not_active IP Right Cessation
- 1983-01-17 NL NL8300159A patent/NL8300159A/nl not_active Application Discontinuation
- 1983-01-19 NZ NZ203056A patent/NZ203056A/en unknown
- 1983-01-19 ES ES519108A patent/ES519108A0/es active Granted
- 1983-01-19 CH CH5162/83A patent/CH657848A5/de not_active IP Right Cessation
- 1983-01-19 PT PT76110A patent/PT76110B/pt not_active IP Right Cessation
- 1983-01-19 IL IL67715A patent/IL67715A/xx not_active IP Right Cessation
- 1983-01-19 AU AU10611/83A patent/AU565538B2/en not_active Ceased
- 1983-01-19 GB GB08301383A patent/GB2113682B/en not_active Expired
- 1983-01-19 DK DK020983A patent/DK161071C/da not_active IP Right Cessation
- 1983-01-19 WO PCT/CH1983/000008 patent/WO1983002610A1/en unknown
- 1983-01-20 HU HU83189A patent/HU189215B/hu not_active IP Right Cessation
- 1983-01-20 IE IE115/83A patent/IE54878B1/en not_active IP Right Cessation
- 1983-01-20 IT IT47588/83A patent/IT1197546B/it active
- 1983-01-20 CA CA000419841A patent/CA1191857A/en not_active Expired
- 1983-01-20 SE SE8300289A patent/SE453293B/sv not_active IP Right Cessation
- 1983-01-20 AT AT0017483A patent/AT381490B/de not_active IP Right Cessation
-
1985
- 1985-01-17 US US06/458,443 patent/US4622336A/en not_active Expired - Fee Related
-
1986
- 1986-01-11 PH PH28376A patent/PH22848A/en unknown
- 1986-12-30 MY MY467/86A patent/MY8600467A/xx unknown
-
1988
- 1988-04-05 SG SG226/88A patent/SG22688G/en unknown
- 1988-04-27 KE KE3813A patent/KE3813A/xx unknown
- 1988-07-28 HK HK568/88A patent/HK56888A/xx unknown
- 1988-09-02 CY CY1431A patent/CY1431A/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |